Acrylic composition and a curable coating composition including the same

Abstract

An acrylic composition includes the reaction product of an acrylic polymer, a carbamate having anhydride-reactive functionality and carbamate functionality, and a carboxylic acid anhydride that is reactive with the carbamate to form a carboxylic acid carbamate. The acrylic polymer includes the reaction product of a functionalized monomer, a first compound reactive with the functionalized monomer to form a functionalized intermediate, and a highly branched, polyfunctional core molecule reactive with the functionalized intermediate. The first compound includes vinyl functionality reactive with the functionalized monomer and epoxy functionality. The carboxylic acid carbamate has the carbamate functionality and carboxylic acid functionality that is reactive with the acrylic polymer. The acrylic composition is highly-branched and, when used in coating compositions in combination with a suitable cross-linking agent, enhances recoat adhesion and produces cured films that have optimum scratch, mar, and chip performance, and acid etch resistance.

1. An acrylic composition comprising the reaction product of:
 A) an acrylic polymer comprising the reaction product of;
 i) a functionalized monomer; 
 ii) a first compound reactive with said functionalized monomer to form a functionalized intermediate, said first compound comprising vinyl functionality reactive with said functionalized monomer and epoxy functionality; and 
 iii) a highly branched, polyfunctional core molecule reactive with said functionalized intermediate to form said acrylic polymer; and 
 
 B) a carboxylic acid carbamate having carbamate functionality and carboxylic acid functionality that is reactive with said epoxy functionality of said acrylic polymer to form said acrylic composition. 
 
     
     
       2. An acrylic composition as set forth in  claim 1  wherein said carboxylic acid carbamate comprises the reaction product of a carbamate having anhydride-reactive functionality and a carboxylic acid anhydride reactive with said anhydride-reactive functionality of said carbamate. 
     
     
       3. An acrylic composition as set forth in  claim 2  wherein said anhydride-reactive functionality is further defined as at least one of hydroxyl functionality and amino functionality. 
     
     
       4. An acrylic composition as set forth in  claim 2  wherein said carboxylic acid anhydride is selected from the group of maleic anhydride, hexahydrophthalic anhydride, methyl-hexahydrophthalic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, succinic anhydride, dodecenylsuccinic anhydride, trimellitic anhydride, glutaric anhydride, and combinations thereof. 
     
     
       5. An acrylic composition as set forth in  claim 2  wherein the ratio of effective equivalents of said carbamate to said carboxylic acid anhydride is from 0.5:3 to 3:0.5. 
     
     
       6. An acrylic composition as set forth in  claim 1  wherein said functionalized monomer comprises hydroxyl-reactive functionality and vinyl functionality. 
     
     
       7. An acrylic composition as set forth in  claim 6  wherein said first compound is selected from the group of glycidyl acrylate, glycidyl alkacrylates, and combinations thereof. 
     
     
       8. An acrylic composition as set forth in  claim 6  wherein said core molecule comprises a polyol reactive with said functionalized intermediate to form said acrylic polymer. 
     
     
       9. An acrylic composition as set forth in  claim 8  wherein said polyol is selected from the group of glycerol, propylene glycol, erythritol, pentaerythritol, dipentaerythritol, trimethylolethane, trimethylolpropane, dulcitol, threitol, and combinations thereof. 
     
     
       10. An acrylic composition as set forth in  claim 6  wherein said acrylic polymer further comprises the reaction product of an initiator selected from the group of inorganic persulfates, dialkyl peroxides, hydroperoxides, peresters, azo compounds, and combinations thereof. 
     
     
       11. An acrylic composition as set forth in  claim 1  wherein said functionalized monomer comprises hydroxyl functionality and vinyl functionality. 
     
     
       12. An acrylic composition as set forth in  claim 11  wherein said core molecule is selected from the group of isocyanates, isocyanurates, melamines, carboxylic acid halides, and combinations thereof with said core molecule reactive with said functionalized intermediate to form said acrylic polymer. 
     
     
       13. An acrylic composition as set forth in  claim 1  wherein said functionalized monomer comprises a radical-forming portion and hydroxyl functionality. 
     
     
       14. An acrylic composition as set forth in  claim 13  wherein said first compound is selected from the group of glycidyl acrylate, glycidyl alkacrylates, and combinations thereof. 
     
     
       15. An acrylic composition as set forth in  claim 13  wherein said core molecule is selected from the group of isocyanates, isocyanurates, melamines, carboxylic acid halides, and combinations thereof with said core molecule reactive with said functionalized intermediate to form said acrylic polymer. 
     
     
       16. An acrylic composition as set forth in  claim 1  wherein said functionalized monomer comprises a radical-forming portion and hydroxyl-reactive functionality. 
     
     
       17. An acrylic composition as set forth in  claim 16  wherein said first compound is selected from the group of glycidyl acrylate, glycidyl alkacrylates, and combinations thereof. 
     
     
       18. An acrylic composition as set forth in  claim 16  wherein said core molecule comprises a polyol reactive with said functionalized intermediate to form said acrylic polymer. 
     
     
       19. An acrylic composition as set forth in  claim 1  wherein said acrylic polymer further comprises the reaction product of a second compound comprising vinyl functionality and reactive with said functionalized monomer and said first compound to form said functionalized intermediate. 
     
     
       20. An acrylic composition as set forth in  claim 19  wherein said second compound is selected from the group of acrylates, methacrylates, acrylonitriles, styrenes, alkemes, cyclic alkene anhydrides, acyclic alkene anhydrides, and combinations thereof. 
     
     
       21. An acrylic composition comprising:
 A) an acrylic polymer comprising the reaction product of:
 i) a functionalized monomer; 
 ii) a first compound reactive with said functionalized monomer to form a functionalized intermediate, said first compound comprising vinyl functionality reactive with said functionalized monomer and epoxy functionality; and 
 iii) a highly branched, polyfunctional core molecule reactive with said functionalized intermediate to form said acrylic polymer; and 
 
 B) a carbamate having anhydride-reactive functionality and carbamate functionality. 
 
     
     
       22. An acrylic composition as set forth in  claim 21  further comprising a carboxylic acid anhydride reactive with said anhydride-reactive functionality of said carbamate to form a carboxylic acid carbamate having said carbamate functionality and carboxylic acid functionality that is reactive with said epoxy functionality of said acrylic polymer. 
     
     
       23. An acrylic composition as set forth in  claim 22  wherein said functionalized monomer comprises α,α-dimethyl isopropenyl benzyl isocyanate, said first compound comprises glycidyl acrylate or glycidyl methacrylate, said core molecule comprises pentaerythritol, said carbamate comprises hydroxypropyl carbamate, and said carboxylic acid anhydride comprises hexahydrophthalic anhydride. 
     
     
       24. An acrylic composition as set forth in  claim 22  wherein said functionalized monomer comprises di-(1-hydroxycyclohexyl) peroxide, said first compound comprises glycidyl acrylate or glycidyl methacrylate, said core molecule comprises trimethylol propane carbamate with tolylene diisocyanate or pentaerythritol carbamate with tolylene diisocyanate, said carbamate comprises hydroxypropyl carbamate, and said carboxylic acid anhydride comprises hexahydrophthalic anhydride. 
     
     
       25. An acrylic composition comprising:
 A) an acrylic polymer comprising the reaction product of:
 i) a functionalized monomer; 
 ii) a first compound reactive with said functionalized monomer to form a functionalized intermediate, said first compound comprising vinyl functionality reactive with said functionalized monomer and epoxy functionality; and 
 iii) a highly branched, polyfunctional core molecule reactive with said functionalized intermediate to form said acrylic polymer; and 
 
 B) a carboxylic acid anhydride. 
 
     
     
       26. An acrylic composition as set forth in  claim 25  wherein said carboxylic acid anhydride is selected from the group of maleic anhydride, hexahydrophthalic anhydride, methyl-hexahydrophthalic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, succinic anhydride, dodecenylsuccinic anhydride, trimellitic anhydride, glutaric anhydride, and combinations thereof.